5-Nitrobenzimidazole → 5-Aminobenzimidazole

HRID 429278Notes

Reaction equation

HRID 429278 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=1)([O-])=O>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 71955-Nitrobenzimidazole

Product 1

HCID 136235-AminobenzimidazoleYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-nitrobenzimidazole (1 g, 6.13 mmol, 1 eq) in THF (100 mL) was added 10% palladium on carbon (385 mg). The flask was purged with H2 and the mixture was stirred under a balloon of H2 for several hours. The flask was purged with N2. The catalyst was filtered and washed with MeOH. The solution was concentrated under reduced pressure giving 800 mg of the desired product.

Workup

  1. customThe flask was purged with H2
  2. customThe flask was purged with N2
  3. filtrationThe catalyst was filtered
  4. washwashed with MeOH
  5. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cd323892bc184908bba1d7e36475fa74
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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